Middleburg was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman John Leven Powell, who purchased the property from Joseph Chinn, a cousin of George Washington. Powell changed the name from “Chinn’s Crossroads” to Middleburg because the town was the halfway point between Alexandria and Winchester along the popular Ashby Gap trading route, along what is today Rte. 50.
The town has a rich history, including serving as the site of two skirmishes in 1863 as part of the Gettysburg Campaign during the Civil War. After the turn of the century, the town became a popular destination for foxhunting and steeplechasing, earning it a reputation as the “Nation’s Horse and Hunt Capital” and attracting well-known visitors from all over the country, including President John F. Kennedy.
With more than 160 buildings listed on the National Register of Historic Places, Middleburg is known for its natural beauty, historic charm, and Southern hospitality. Surrounding the town, you’ll find picturesque countryside, with low stone walls surrounding stately horse farms and cattle grazing in nearby fields–all with the Blue Ridge and Bull Run mountains as a scenic backdrop. With an ideal climate for growing grapes, Middleburg also boasts more than 20 wineries within 30 minutes of this historic hamlet, making it one of the top 10 wine destinations in the world.
